Keto-alcohol



uctof the reaction of acetone with methyl ethyl Patented Sept. 12, 1933 nErro-ALoonoL Robert H. Van Schaack, J11, Evanston, 111., as-

signor to 'Van SchaackBros. Chemical Works, 1110., Chicagmlllh, aoorporation of Illinois I Ne Drawing.

Application December 17. 1 929, Serial N0.'414,832

5 Claims. (Cl. 260-434).

This invention relates to keto-alcohols andparticularly to products ofth'e condensation of acetone with methyl ethyl ketone andhigher ,ketones'.

The invention may be illustrated by the prod ketone in'the presence of an alkaline condensing Y agent. The reaction product comprises 4-hydroxy--methyl-Z-hexanone,

d r and its isomer, 5-hydroXy-5-methyl-3-hexanone.

The proportion of the two isomers formed may vary with the conditions of the reaction. Also, one isomer may be formed practically to'the exclusion or" the other.

Details of anillustrative method for preparing these ketones follow.

acetone is agitated with one or. two molecular I proportions of methyl ethyl ketone and a small amount of caustic sodathat hasbeen finely ground with twice its weight of precipitated" calcium carbonate. :"Ihe amount of the ground mixture of alkali and calcium carbonate used is suitably five parts by weight to one thousand parts of the ketones. The temperature at which the agitation is mademay be below C; The agitation is continued for suflicient time to cause the reaction of a substantial "amount of the ace-- tone with methyl ethyl ketone, to give a product of higher specific gravity and higher boiling point than either of the original ketonesa Thus. I have continued: the agitation for twenty-two. hours." During these twenty-two hours agitation, liquid '-was continuously filtered from the mixture and delivered to an evaporator containing succinic acid in excess of the alkali dissolved in the illtered liquor and maintained, at a temperature above the boiling point methyl ethyl ketone The resulting vapors, comprising unreaoted aca tone and methyl ethyl ketone were passed through a condenser and the condensate there-i from returned to, the reaction vessel. In this means of adraw-off valve. After twenty-two hours reaction as above described, approximately 40% of the weight of the original ketones'was "obtained in the form of a fractionof high boil-,

these reactions are accelerated by heat. I

mg Point T s was then submitted to 1 3 distillation, in a yacuum, to removea foreshot comprising acetone and methyl ethyl ketone that 'had not been distilled away during the continu ousevaporation of liquid filtered'froin the rea action vessel. The residue from this distillation comprises the. keto-alcohols (substituted hexanones) of the formulas given above.

'The process'may be applied to the manufac ture of other keto-alcohols, i1" the'methyl ethyl.

ketone, used in the above example, is substituted by an equi-molecular proportion of a higher ketone; in this manner I may make keto-alcohols of the general type formula groups otherthan the methyl may be ethyl, isopropyl, propyl, butyl, secondary butyl, amyl,'or- One molecular proportion of substantially dry' other alkyl radical containing at least'two carbon atoms.

The keto alcohols invented by me are useful s5 tilled at atmospheric pressure without decomposition, particularly if a trace 'oi.a1kali is present.

If distilled under a pressureoi 22 mm. of mere cu-ry these compounds boil at temperatures above 66 C. The keto-alcohols are resolved into their constituent ke'tones upon treatment with an alkali. Decomposition alsoresults when they are broughtinto contact with astrong'acid. Both V It will be understood that methods of preparation other than the one given may be used in the preparation of the keto-alcohols.

. When the method of preparation is that offcondensation in the presence of an alkali, the alkali 'usedmaybe hydratedlime or finely ground sodium or potassium hydroxide, suitably mixed with adistending agent, as, for examplacalcium carbonate or calcium sulfate. The amount of al kali used may be about 10% ofthe weight of 1 e-. tones, whenflimeis used, or (Hi2 to 2.0% when finely ground caustic alkalies are used. Thetem perature of reaction may besomewhat "above or below atmospheric, as, for example, 50to '20 0., i Q 7 say, 0C. The continuous process described may be substituted by'a batch process in which the 1m .80?! in pyroxylin compositions. Those made from the mixture of ketones is treated with the alkaline condensing agent until equilibrium in the reaction is'approached, the mixture then filtered to remove undissolved alkali, the filtrate neutralized or made slightly acidic with a weakiacid, such as suocinic, and the neutralized liquid then' distilled to remove low boiling ingredients and leave a residue comprising keto-alcohols.

By the term keto-alcohol, as used in the specification and claims, I mean a compound containing both the ketone and the alcohol group,

- which is not.

as illustrated in the formulas above.

I claim: i, 1. A kcto-alcohol of the formula CH3 l 7 2. A keto-al coholv whose composition may .be represented by the general formula in which the His represent alkyl groups, at least and another of;

one of which is the'methyl group 3. A keto-alcohol whose composition may be two are methyl groups and the other is the'ethyl v group. I

5. A keto-alcohol whose composition may be represented by the general formula v R 7 r OQHOHz-CO,-R, R

ferentalkyl groupf t RQBERT H. VANv SCHAACK,'J R.

which the Rs represent alkyl groups of which; two are methyl groups and the other is a dif- 

